Parasiticidal preparation



Patented Nov. 17, 1942 2,302,384 rmsmcmm. PREPARATION William P. ter Horst, Packanack Lake, N. J., 88-

signor to United States Rubber Company, New York, N. Y., a corporation of New Jersey No Drawing.

Application July 11, 1939,

Serial No. 283,817

8 Claims.

This invention relates to new and useful improvements in parasiticidal preparations.

More particularly the invention relates to parasiticides which may be used as fungicides, seed protectants, insecticides, insect repellents, or bactericides.

This case is a continuatlon-in-part of my application Serial No. 234,962, filed October 14, 1938.

The parasiticides include quinone-oxime type compounds in which a quinone nucleus is doubly bonded to each of two nitrogen atoms, the remaining valency of each nitrogen atom being satisfied by oxygen. They may be used in the form of sprays or dusts, alone or in combination with other fungicides or insecticides, or in combination with fertilizers or with suitable auxiliary agents such as wetting agents, sticking agents, spreading agents, etc.

While some of the compounds have outstanding value as fungicides, other of the compounds have outstanding insecticidal value including their use as stomach poisons or as insect repellents for such pests as the Mexican bean beetle, Southern army worm, Colorado potato beetle, etc. This latter is particularly true of orthobenzoquinone dioxime, and para-benzoquinone dioxime.

As a seed protectant or fungicide the product obtained by .mlld oxidation of ortho-nitraniline with sodium hypochlorite in known manner, and which may be called ortho-benzoquinone dioxime peroxide, has outstanding value. It greatly assists in controlling the phenomenon which is usually called damping ofi which causes a decrease in the percentage of germination, low speed of emergence, and non-vigorous plants due to soilfungi which are harmful to the seed and the sprout, such as the Pythium spore, the Fusarium spore, and the Rhizoctania. spore. The said oxidation product also functions as a lubricant for the seed resulting in less interlocking of the seeds in the feed drill and in less damage to the seed and to the equipment. This is in contrast with most of the chemical dusts that are used commercially at the present time as most of those increase the friction.

The tests tabulated below demonstrate the effectiveness of the new fungicides in preventing spore germination. The tests were carried out as follows:

An aqueous solution or suspension of the chemical to be tested containing grams thereof per liter of water was prepared. This solution or suspension was sprayed on glass slides which had previously been coated with nitrocellulose.

An atomizer was used capable of delivering 10 cc. spray liquid in 36 seconds. A glass slide was positioned two feet away from the nozzle of the atomizer. Spraying was carried out for, respectively, 3 seconds, 5 /2 seconds, 8 seconds, 10 /2 seconds and 13 seconds. The spray deposit was allowed to dry. The test organism, for example Macrosporium Sarcinaeforme was then inoculatedon the sprayed slide and germination was allowed to take place in a moist chamber at 25 C. On the untreated slides usually approximately 98% of the spores germinated.

Per cent spore germination Chemical 3" 5% 8" 10% 18" p-Beuzoquinone dioxime 49. 0 32. 3 6. 3 3. 7 0. 0 o-Benzoqulnone dioxime 4. 3 4. 0 4. 0 4. 0 4. 0 Sodium salt of p-benzoquinonedloxime. 89. 0 76. 7 48. 3 16.0 17. 0 Zinc salt of p-beuzoquinone dioxime ll. 3 8. 3 6. 7 5. 7 2. 3 Sulfurized p-benzoquinone'dioxime 81. 3 34. 0 6. 0 6. 0 3. 0 p-Benzoquinone dioxime dimethyl ether- 94. 3 97. 0 94. 0 90. 0 66. 7 Zinc salt of thymoquinone dioxime 26. 0 9. 7 0 0 0 o-Benzoquinone dioxime peroxide 4. 0 0 0 O 0 It was also found that para-b'enzoquinone-dioxime was very effective in preventing fungus growth of a number of other fungi such as Coccomyces hiemalisQRhizopus nigricans, Penicillium spore, Aspergillus spore, Phoma spore, etc. The effectiveness of the aforesaid oxidation product of ortho-nitraniline as an organic seed Average Emergence Emergence height of after 7 after 23 sprout days days after 23 days Percent Percent Centimeterc Untreated seed 21 61 i0. 0 Seed treated with 25% of the sodium hypochlorite oxidatipn roduct of orthomtr e 51 87. 0 i4. 28-

A similar test made in soil artificially inoculated with Sclerotina spore gave the following results: V

Lima bean seed was planted in soil that was known to have a high damping off" potentialwith the following results:

Av. Emerg- Emerg- Emergheight of once after once after enoe alter s rout 7 days 14 days 23 days ter 23 days Per cent Per cent Per cent Untreatedseed 3 8 14 10.2 Seed treated with 35% of the sodium hypochlorite oxidation prodnot of ortho-nitraniline- Q 26 46 17.

Instead of the aforesaid oxidation product of o'rtho-nitraniline, there may be used the analogous oxidation products of para-nitraniline and in general of other orthoor para-nitro substituted amines such as nitro toluidines, nitr;o naphthylamines, etc. Other related compounds may beused such as 3,4-benzofurazane which can be made by dehydrating orthobenzoquinone dioxime; para-benzoquinone dioxime peroxide MAI para-benzoquinone dioxime anhydride Other compounds falling within the scope of the invention are p-benzo-quinone dioxime bis acetate (anti-form) p-benzequinone dioxime bis acetate (syn form), copper salt of p-benzoquinone dioxime, diquinoyl-tetroxime, -chloro-orthoquinone dioxime' peroxide, the ,naphthoquinone dioximes, the toluquinone dioximes, the xyloquinone dioximes, the anthraquinone dioximes, and their derivatives corresponding to the above, illustrated in connection with the benzoquinone dioximes; metallic salts other than those particular1y.mentioned above, such as potassium, ammonium, mercury, magnesium and calcium salts: halogen-substituted dioximes in which halogen replaces hydrogen of the benzene ring, such as monochloro-orthoquinone di--oxime; tetrachloro-p-benzoqulnone dioxime; diquinoyl dioxime; naphthoquinone dioxirne peroxides; naphthoquinone dioxime anhydrides.

The materials described herein may be applied undiluted, or suspended in water or other vehicle, or mixed with talc, clay and the like, or as aforesaid may be used in admixture with other parasiticidal chemicals.

Having thus described my invention, what I claim and desire to protect by Letters Patent is:

1. A bactericide, fungicide, and insecticide preparation containing as an.active constituent a quinone dioximino compound.

2. A bactericide, fungicide, and insecticide preparation containing as an active constituent a benzoquinone dioxime; U

3. A bactericide, fungicide, and insecticide preparation containing as an .active constituent ortho benzoquinone dioxime.

4. A bactericide, fungicide, and insecticide preparation containing as an active constituent an oxidation product of-a nitro substituted aromatic amine, said product having a quinone nucleus doubly bonded to each of two nitrogen atoms.

5. A bactericlde, fungicide, andinsecticide preparation containing as an active constituent ortho benzoquinone dioxime peroxide.

6. A bactericide, fungicide, and insecticide preparation containing as an active ingredient a benzene compound having each of two nitrogen atoms doubly bonded to the benzene nucleus both of said nitrogen atoms being additionally bonded to oxygen.

' 7. A bactericide, fungicide, and insecticide preparation containing as an active constituent para-benzoquinone dioxime.

8. A fungicide preparation containing as an active constituent an oxidation product of orthonitraniline, said product having a quinone nucleus doubly bonded to each of. two nitrogen atoms.

WILLIAM P. :rsa HORST. 

